Yamsickle originally joined Cumball in March 2025, but first appeared on cunny.zone weeks earlier where he would stream himself playing games and doing other activities live for a single-digit number of viewers. Although his exact origin is unknown, his association with Alternative Entertainment leads many to believe that he found about cunny.zone and Cumball through them.

It's unknown exactly when Yamsickle began creating content on the internet, but he began creating content on cunny.zone in early 2025. He is a self-proclaimed streamer with many years of experience and an avid VRChat player, and VR enthusiast who has been smitten with both for over 5 years. His VRChat account is over 7 years old.

Yamsickle started livestreaming on cunny.zone's predecessor icunny.com through Filled With Nothing's page on the site on March 6, 2025. In his first livestream, he would play Halo 2 and introduce himself to the 2 or so viewers that were present and stream for a few hours. After his first stream, he would stream himself playing Halo 2 again on March 7 and 9, and would end the month of March streaming himself playing ENA: Dream BBQ on the 27th. He would take a de facto 2-month hiatus after the ENA stream and then stream on June 4, playing a VR game on stream for the first time. His final stream as an independent would happen on the 28th of July, where he would be playing Halo 2.

After iCunny.com was closed and replaced with cunny.zone, Yamsickle would stream on the new site on October 22, 2025 doing a “VRChat test stream”, there he would go around in VRChat testing to see if it would attract more than a single-digit number of viewers, to no avail. It's in this stream that he would reveal that he was officially associated with Alternative Entertainment, and that he was collaborating with them on a new debut of his character.

This Yamsickle VTuber debut began development in November and would encounter many difficulties and obstacles early on in its development which were attributed to the group's lack of experience in 3D modeling, lack of voice actors, and good texture artists. Despite the whole debut stream being planned out, other performers having been convinced to show up, and custom 3D assets nearing completion, the whole thing was scrapped for not meeting AE's strict quality standards, much to Yamsickle's dismay.

The debut stream was planned to air on November 30 2025, then delayed to April 12 2026, and then finally cancelled altogether. As a form of consolation, Yamsickle would promise to stream almost daily on his channel starting on April 13. These Consolation Week streams, however did not take place in one week and instead took place sporadically throughout 3 separate months.

Yamsickle's first stream of 2026 was on January 4, 2026 where he would reveal many things that were being worked on behind the scenes for him and within Alternative Entertainment. Due to the sensitive nature of the topic being discussed, he had to be very careful as to what to reveal and what not to reveal during the stream. After this stream, he wouldn't stream for 3 months and 9 days, the longest de facto hiatus Yamsickle has ever had from streaming. He would break this hiatus when he streamed his Consolation Week streams on April 13, April 14, then May 2, 3, 4, 5, then May 12, and then finally ending on June 6, 2026. His most recent stream since then has been on July 18 2026.

Yamsickle has not streamed on cunny.zone since July 18, 2026. The exact reason is unknown, but many have assumed he has stepped away from streaming due to the consistent lack of viewership, the fact that he has full-time employment, and more recently, his undertaking of creating a solar-powered mobile shed for himself to live in.

As of writing, it has been 3 months, and 9 days since his last stream, matching the time of his previous hiatus. Despite being absent from cunny.zone, he is still active on Discord and is planning to make a Twitch or Kick channel to continue streaming.

Yamsickle plans to create his own website, become a streamer with at least a thousand concurrent viewers, and make YouTube videos about things that spark his interest like VR and IT.

Yamsickle.live is a planned personal website hosted and created by Yamsickle that will host high quality footage from his YouTube videos, VODs from his streams, and links to all of his social media accounts present and/or active on the internet. He also has shared plans to stream from there, but has not elaborated on that plan nor officially confirmed it more than once.